Baltimore, Md (WBFF) - For Baltimore City Comptroller Joan Pratt, a looming Department of Labor investigation was bad enough, factor in the shredding of documents by a former high-ranking employee and Pratt's problems just became more complicated.

FOX45 wanted to find out if the shredding itself might result in criminal charges.

Experts tell us timing is everything.

Remember this investigation already dates back several months.

It came after employees within the Comptroller's Office complained they were being forced to work unpaid overtime.

Online the Department of Labor lays out the steps of an investigation.

First, there's the examination of records to determine which laws or exemptions apply.

Next, payroll and time records are examined.

Photocopied if necessary.

Employees are interviewed.

Lastly, the employer is questioned.

We already know employees have been questioned which according to the Department of Labor would mean all the necessary records have likely been obtained.

How this might end for Joan Pratt is hard to say.

What we do know is there are questions and practices involving the Comptroller's Office that have raised concerned.

And, those concerns are serious enough for the DOL to investigate.

Watch Related Story|| Comptroller Under Investigation 

We also know the shredding has led Acting City Solicitor Dana Moore to ask Baltimore’s Inspector General to investigate the actions of former 

Acting City Solicitor says|| 

My understanding is that Ms. Taylor was in City Hall for a total of 8 to 12 hours over the course of Thursday afternoon into the evening and, Friday morning.

Moore tells Fox45||

I have no idea how long shredding was actually happening.